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WO1999023999A2 - Utilisation de melanges pour la fabrication de demaquillants - Google Patents

Utilisation de melanges pour la fabrication de demaquillants Download PDF

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Publication number
WO1999023999A2
WO1999023999A2 PCT/EP1998/006897 EP9806897W WO9923999A2 WO 1999023999 A2 WO1999023999 A2 WO 1999023999A2 EP 9806897 W EP9806897 W EP 9806897W WO 9923999 A2 WO9923999 A2 WO 9923999A2
Authority
WO
WIPO (PCT)
Prior art keywords
alcohols
fatty
linear
monoglyceride
esters
Prior art date
Application number
PCT/EP1998/006897
Other languages
German (de)
English (en)
Other versions
WO1999023999A3 (fr
Inventor
Armin Wadle
Catherine Le Hen-Ferrenbach
Original Assignee
Cognis Deutschland Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Priority to AU15584/99A priority Critical patent/AU1558499A/en
Priority to EP98959817A priority patent/EP1028696B1/fr
Priority to DE59805343T priority patent/DE59805343D1/de
Publication of WO1999023999A2 publication Critical patent/WO1999023999A2/fr
Publication of WO1999023999A3 publication Critical patent/WO1999023999A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up

Definitions

  • the invention relates to the use of mixtures containing monoglyceride (ether) sulfates, oil bodies and optionally fatty alcohols for the production of make-up removing agents.
  • a typical makeup composition contains, for example, glycerol monostearate, cetyl alcohol, stearic acid, paraffin oil, cetyl stearyl octanoate, octyl palmitate, talc, titanium dioxide, iron oxides, propylene glycol, polysorbates, xanthan, magnesium aluminum silicate, glycerin, perfume oils, preservatives and water.
  • Mascara or wax contains mascara, dyes, emulsifiers and thickeners. In addition to dyes, waxes and oil bodies, lipsticks also contain mica titanium dioxide and, more recently, silicone compounds.
  • Eyeshadows are usually mixtures of dyes with mica or titanium dioxide, which can contain talc, paraffin oil, kaolin, metal soaps, wax alcohols and emulsifiers as further ingredients.
  • Kajal pencils contain, for example, iron oxides, vegetable oils, waxes, fatty acids, talc and emulsifiers.
  • Corresponding cosmetic cleaning agents must therefore remove a large number of completely different substances as completely as possible from the skin, i.e. dissolve typical waxes, oils and silicone compounds and at the same time also solubilize pigments such as mica or titanium dioxide. Furthermore, they have to be as mild as possible to prevent reddening of the skin or even irritation to the eyes.
  • German patent application DE-A1 19605360 (Henkel) relates to emulsions with particularly high storage stability, which contain monoglyceride (ether) sulfates, emulsifiers and chitosans.
  • ether monoglyceride
  • the complex object of the present invention was to provide new skin cleansing agents in emulsion form which have a high cleaning ability against waxes, oils, silicone compounds and also against pigments, are extremely compatible with the skin and mucous membranes and at the same time have a particularly high storage stability have.
  • the invention relates to the use of mixtures containing
  • mixtures of monoglyceride (ether) sulfates and oil bodies have a high cleaning ability for waxes, oils and pigments and, in particular, silicone compounds, are well tolerated by the skin and eye mucous membranes and, in particular, do not separate in the heat.
  • the invention includes the finding that the storage stability of the binary mixtures is further improved by adding fatty alcohols; at the same time, the consistency of the preparations is increased.
  • Monoglyceride sulfates and monoglyceride ether sulfates are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry.
  • the usual starting point for their preparation is triglycerides, which, if appropriate, are transesterified to the monoglycerides after ethoxylation and subsequently sulfated and neutralized.
  • partial sulfating agents preferably gaseous sulfur implement trioxide or chlorosulfonic acid [cf. EP-B1 0561825, EP-B1 0561999 (Henkel)].
  • the neutralized substances can be subjected to ultrafiltration in order to reduce the electrolyte content to a desired level [DE-A1 4204700 (Henkel)].
  • Overviews of the chemistry of the monoglyceride sulfates are, for example, by AKBiswas et al. in J.Am.Oil.Chem.Soc. 37, 171 (1960) and FUAhmed J.Am.Oil.Chem.Soc. 67, 8 (1990).
  • the monoglyceride (ether) sulfates to be used in accordance with the invention follow the formula (I),
  • R 1 CO stands for a linear or branched acyl radical with 6 to 22 carbon atoms, x, y and z in total for 0 or for numbers from 1 to 30, preferably 2 to 10, and X stands for an alkali or alkaline earth metal.
  • Typical examples of monoglyceride (ether) sulfates which are suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, cetylstearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid formaldehyde sulfuric acid trioxide with their sulfuric acid trioxide sulfate formate.
  • Monoglyceride sulfates of the formula (I) are preferably used in which R 1 CO is a linear acyl radical having 12 to 14 or 16 to 18 carbon atoms.
  • Fatty alcohols are to be understood as primary aliphatic alcohols of the formula (II)
  • R 2 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
  • Typical examples are cappa alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroseiyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl
  • fatty alcohols with 12 to 18 carbon atoms such as coconut, palm, palm kernel or tallow fatty alcohol are preferred.
  • fatty alcohols are used which have the same fat residue as the monoglyceride (ether) sulfates, for example cetylstearyl alcohol in combination with cetylstearic acid monoglyceride sulfate.
  • Another object of the invention relates to the use of mixtures containing
  • the agents produced using the mixtures generally have a water content of 10 to 90, preferably 20 to 70% by weight and can be present both as low-viscosity, sprayable emulsions with droplet sizes of the oil phase of ⁇ 2 ⁇ m or as creams.
  • suitable carriers such as, for example, cotton wool or viscose, are impregnated with the preparations for the production of eye cleansing agents or make-up removal wipes and are thus brought onto the market.
  • the preparations obtainable using the mixtures can furthermore contain, as auxiliaries and additives, mild surfactants, co-emulsifiers, superfatting agents, stabilizers, consistency agents, thickeners, silicone compounds, biogenic active substances, preservatives, hydrotropes, solubilizers, perfume oils, dyes and the like contain.
  • Suitable mild, i.e. surfactants which are particularly compatible with the skin are fatty alcohol polyglycol ether sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkyl amide betaine acids and / or protein fats, and protein fats, based on the latter, and / or protein based fatty acids, and / or protein based fatty acids, and / or protein based fatty acids, and / or protein based fatty acids, and / or protein based fatty acids, and / or protein based fatty acids, and / or protein based fatty acids.
  • suitable co-emulsifiers are nonionic surfactants from at least one of the following groups:
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polystyrene resin e.g. Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
  • partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside - glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homolog mixtures, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C12 / 18 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • C ⁇ / 18 alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C12 / i ⁇ -acylsarcosine.
  • Quaternary emulsifiers are also considered, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and di-esters of fatty acids, polyacrylates, (for example Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar a
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides, waxes include Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or micro waxes, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question.
  • Metal salts of fatty acids such as e.g.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes to understand.
  • Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases.
  • Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
  • glycerin • Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and poly ethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides especially those with 1 to 8 carbons in the alkyl radical such as methyl and butyl glucoside;
  • Sugar alcohols having 5 to 12 carbon atoms such as, for example, sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Perfume oils include extracts from flowers (lavender, roses, jasmine, neroli), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway seeds, juniper), fruit peels (bergamot, lemon, oranges), roots (Macis, Angeiica, Celery, Cardamom, Costus, Iris, Calmus), woods (sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemon-grass, sage, thyme), needles and branches (spruce , Fir, pine, mountain pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Animal raw materials such as musk, civet and castoreum are also suitable.
  • Ambroxan, eugenol, isoeugenol, citronellal, hydroxycitronellal, geraniol, citronellol, geranyl acetate, citral, ionone and methylionone are suitable as synthetic or semi-synthetic perfume oils.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used. Examples

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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Abstract

L'invention concerne l'utilisation de mélanges détergents, contenant (a) des monoglycérid(éther)sulfates et (b) des corps huileux, pour la fabrication de démaquillants sous forme d'émulsion pour les yeux et les parties cutanées sensibles.
PCT/EP1998/006897 1997-11-10 1998-10-30 Utilisation de melanges pour la fabrication de demaquillants WO1999023999A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU15584/99A AU1558499A (en) 1997-11-10 1998-10-30 Use of mixtures for producing make-up removers
EP98959817A EP1028696B1 (fr) 1997-11-10 1998-10-30 Utilisation de melanges pour la fabrication de demaquillants
DE59805343T DE59805343D1 (de) 1997-11-10 1998-10-30 Verwendung von mischungen zur herstellung von abschminkmitteln

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19749550.8 1997-11-10
DE19749550A DE19749550A1 (de) 1997-11-10 1997-11-10 Verwendung von Mischungen zur Herstellung von Abschminkmitteln

Publications (2)

Publication Number Publication Date
WO1999023999A2 true WO1999023999A2 (fr) 1999-05-20
WO1999023999A3 WO1999023999A3 (fr) 1999-07-15

Family

ID=7848123

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006897 WO1999023999A2 (fr) 1997-11-10 1998-10-30 Utilisation de melanges pour la fabrication de demaquillants

Country Status (4)

Country Link
EP (1) EP1028696B1 (fr)
AU (1) AU1558499A (fr)
DE (2) DE19749550A1 (fr)
WO (1) WO1999023999A2 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1500775A (fr) * 1965-06-08 1967-11-10 Procédé pour la préparation de produits de nettoyage, notamment à usage épidermique, ainsi que les produits conformes à ceux obtenus par le présent procédé ou procédé similaire
US4806572A (en) * 1987-05-04 1989-02-21 Creative Products Resource Asociates, Ltd. Hydrophilic foam pad for makeup removal
US5011681A (en) * 1989-10-11 1991-04-30 Richardson-Vicks, Inc. Facial cleansing compositions
GB9113517D0 (en) * 1991-06-21 1991-08-07 Procter & Gamble Cleansing products

Also Published As

Publication number Publication date
DE19749550A1 (de) 1999-05-20
WO1999023999A3 (fr) 1999-07-15
DE59805343D1 (de) 2002-10-02
EP1028696B1 (fr) 2002-08-28
AU1558499A (en) 1999-05-31
EP1028696A2 (fr) 2000-08-23

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